368-43-4 Usage
Description
Benzenesulfonyl fluoride, also known as tosyl fluoride, is a clear light yellow liquid with unique chemical properties. It is a derivative of benzenesulfonic acid, where one of the hydrogen atoms is replaced by a fluorine atom. BENZENESULFONYL FLUORIDE is known for its reactivity and is widely utilized in various chemical reactions and processes.
Uses
Used in Chemical Synthesis:
Benzenesulfonyl fluoride is used as a reagent in the chemical synthesis of α-sulfonyl phosphonates. It is particularly effective in the direct sulfonylation of lithiated alkyl phosphonates, which are important intermediates in the preparation of various organic compounds.
Used in Mass Spectrometry:
In the field of analytical chemistry, benzenesulfonyl fluoride has been employed in the study of gas-phase fluorine migration reactions of radical cations. This research has been conducted using electron ionization tandem mass spectrometry, providing valuable insights into the compound's chemical behavior and properties.
Used in Pharmaceutical Industry:
Benzenesulfonyl fluoride is also utilized in the pharmaceutical industry as a protecting group for amines and alcohols during organic synthesis. Its selective reactivity and ease of removal make it a preferred choice for protecting functional groups in the synthesis of complex molecules, including drugs and drug candidates.
Used in Research and Development:
Due to its unique chemical properties, benzenesulfonyl fluoride is often used in research and development for the synthesis of novel compounds and the investigation of various chemical reactions. It serves as a valuable tool for chemists in understanding reaction mechanisms and developing new synthetic routes.
Safety Profile
A poison by
intraperitoneal route. Slightly irritating to
sbn. Flammable when exposed to heat or
flame. It can react vigorously with oxihzing
materials. To fight fire, use water, foam,
CO2, water spray or mist, dry chemical.
When heated to decomposition it emits
toxic fumes of Fand SO,. See also
FLUORIDES and SULFATES.
Check Digit Verification of cas no
The CAS Registry Mumber 368-43-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,6 and 8 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 368-43:
(5*3)+(4*6)+(3*8)+(2*4)+(1*3)=74
74 % 10 = 4
So 368-43-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H5F3Si/c7-10(8,9)6-4-2-1-3-5-6/h1-5H
368-43-4Relevant articles and documents
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Seel et al.
, p. 437 (1978)
-
Copper-Catalyzed Intermolecular Functionalization of Unactivated C(sp3)-H Bonds and Aliphatic Carboxylic Acids
Mao, Runze,Bera, Srikrishna,Turla, Aurélya Christelle,Hu, Xile
supporting information, p. 14667 - 14675 (2021/09/18)
Intermolecular functionalization of C(sp3)-H bonds and aliphatic carboxylic acids enables the efficient synthesis of high value-added organic compounds from readily available starting materials. Although methods involving hydrogen atom transfer have been developed for such functionalization, these methods either work for only activated C(sp3)-H bonds or bring in a narrow set of functional groups. Here we describe a Cu-catalyzed process for the diverse functionalization of both unactivated C(sp3)-H bonds and aliphatic carboxylic acids. The process is enabled by the trapping of alkyl radicals generated through hydrogen atom abstraction by arylsulfonyl-based SOMO-philes, which introduces a large array of C, N, S, Se, and halide-based functional groups. The chemoselectivity can be switched from C-H functionalization to decarboxylative functionalization by matching the bond dissociation energy of the hydrogen atom transfer reagent with that of the target C-H or O-H bond.
Redox-Neutral Organometallic Elementary Steps at Bismuth: Catalytic Synthesis of Aryl Sulfonyl Fluorides
Cornella, Josep,Magre, Marc
, p. 21497 - 21502 (2022/01/03)
A Bi-catalyzed synthesis of sulfonyl fluorides from the corresponding (hetero)aryl boronic acids is presented. We demonstrate that the organobismuth(III) catalysts bearing a bis-aryl sulfone ligand backbone revolve through different canonical organometallic steps within the catalytic cycle without modifying the oxidation state. All steps have been validated, including the catalytic insertion of SO2 into Bi-C bonds, leading to a structurally unique O-bound bismuth sulfinate complex. The catalytic protocol affords excellent yields for a wide range of aryl and heteroaryl boronic acids, displaying a wide functional group tolerance.
